Benzyl Bromide → Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate

HRID 2395070Notes

Reaction equation

HRID 2395070 reaction equation
[OH:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18973722Methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate

Product 1

HCID 18973721Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoateYield 62.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate (1.1 g, 4.3 mmol) in DMF (30 ml) was treated with benzyl bromide (0.89 g, 5.2 mmol) and potassium carbonate (0.72 g, 5.2 mmol). The reaction was stirred at ambient temperature overnight and then, partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2) eluting with CH2Cl2 /EtOAc to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.94 g, 53%) as a low melting yellow solid.

Workup

  1. custompartitioned between EtOAc/water
  2. washThe organic phase was washed well with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2)
  6. washeluting with CH2Cl2 /EtOAc

Sources & evidence

ORD record
ord-4ad259ec389f4581ada1be4e095ffadb
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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